SYNTHESIS OF 10(S)-HYDROXYEICOSATETRAENOIC ACID - A NOVEL CYTOCHROME-P-450 METABOLITE OF ARACHIDONIC-ACID

Authors
YEOLA SN SALEH SA BRASH AR PRAKASH C TABER DF BLAIR IA
Citation
Sn. Yeola et al., SYNTHESIS OF 10(S)-HYDROXYEICOSATETRAENOIC ACID - A NOVEL CYTOCHROME-P-450 METABOLITE OF ARACHIDONIC-ACID, Journal of organic chemistry, 61(3), 1996, pp. 838-841
Citations number
24
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
61
Issue
3
Year of publication
1996
Pages
838 - 841
Database
ISI
SICI code
0022-3263(1996)61:3<838:SO1A-A>2.0.ZU;2-M
Abstract
(-)-hydroxyeicosa-5(Z),8(Z),11(Z),14(Z)-tetraenoic acid methyl ester ( 2) was synthesized in eight steps starting from enantiomerically pure (Ri-glyceraldehyde acetonide. The 10(R)-(+)-enantiomer was prepared us ing an identical method except that the starting material was (S)-glyc eraldehyde acetonide. By use of these authentic standards, it was poss ible to confirm that arachidonic acid was converted to a mixture of (- )-hydroxyeicosa-5(Z),8(Z),11(Z),14(Z)-tetraenoic acid (1) and the 10(R )-(+)-enantiomer by phenobarbital-induced rat Liver microsomes.